Jeffrey Manchester
Jeffrey Manchester eluded police on multiple occasions during his robbery spree, which began in 1998. He earned the nickname “Roofman” because his modus operandi was to enter a business through its roof and then hide in the bathroom. The former U.S. Army soldier was suspected of over three dozen robberies between 1998 and 2000 when he was arrested by North Carolina police. But Manchester wasn’t done: In June 2004, he followed up his two years of crime by escaping from North Carolina’s Brown Creek Correctional Institution.
According to SFGate, Manchester hand-built a wood platform that he attached to the underside of a truck and became the first person to ever break out of Brown Creek. That led him to living in a Toys “R” Us store in Charlotte, N.C., which served as the basis for the Roofman movie. He was arrested in January 2005 after more than six months on the run when he arrived at his girlfriend’s house. Manchester then tried to escape from prison two more times, in 2009 and 2017.
Whitey Bulger
James “Whitey” Bulger remains a notorious figure not only in organized crime history, but for his controversial and messy relationship with the FBI. Bulger was already firmly ensconced in the Boston mob scene when the Bureau tried to recruit him in 1971. FBI agents John Connolly, who had grown up in Bulger’s neighborhood, and John Morris began a relationship with him that saw both agents criminally charged.
In 1994, Connolly informed Bulger that the crime boss was about to be indicted, and Bulger became a fugitive. He was placed on the FBI’s Ten Most Wanted Fugitives List, where he stayed for over a decade, and there was even a separate “Bulger Fugitive Task Force” devoted specifically to his capture. Bulger was finally located in California after 16 years. The FBI press release noted that his arrest came just days after the Bureau had launched a new media campaign to find him. Bulger received two life sentences in 2013 but was murdered in prison in 2018.
Ted Kaczynski
The hunt for the “Unabomber” lasted a whopping 17 years. Ted Kaczynski graduated from Harvard in 1962 after earning a scholarship at 15 years old and earned praise for his graduate work at the University of Michigan. But this mathematics prodigy resigned from teaching in 1969 and committed his first bombing in 1978, on the campus of Northwestern University. In total, he was responsible for 16 bombings between 1978 and 1985, including one that exploded on an American Airlines jet mid-flight in 1979.
Known by the FBI case identifier UNABOM (short for “University and Airline Bomber”), Kaczynski became one of the Bureau’s 10 Most Wanted Fugitives. John Douglas, the agent on whom the TV series Mindhunter is based, wrote a profile on the then-unidentified Kaczynski in 1980. Kaczynski’s own family was also instrumental in the investigation; his brother, David, suspected he was the Unabomber. In 1996, Kaczynski was arrested by the FBI. He pleaded guilty in 1998, was diagnosed with rectal cancer in 2021 and died by suicide in 2023. There was, however, a failed campaign to get him elected president in 1996. SFGate reported that the “Unapack” effort raised “more than $25,000.”
Leonard T. Fristoe
Leonard T. Fristoe holds the Guinness World Record for the longest consecutive amount of time spent as a fugitive after being on the run for 46 years. He murdered Constable Arthur St. Clair and Deputy George Requa of Nevada’s Elk County Sheriff’s Office in 1920. The Officer Down Memorial Page notes that the two officers were ambushed while approaching a stolen car, with St. Clair dying instantly and Requa passing away two weeks later. While Fristoe was sentenced to life in prison in 1920, he escaped custody in 1923—in the warden’s car after driving him to a local brothel. He managed to evade capture for more than four decades, living under the assumed name of Claude R. Willis. But in 1969, Fristoe had an argument with his son, who then turned his father in to police.
Fristoe’s case became even more memorable when, upon his re-arrest, he confessed to a third murder in Texas, which happened shortly after his escape. He was released by the Nevada Parole Board after serving just five months in prison since Fristoe was then in his late 70s. He died in Texas in 1976.
Frank Freshwaters
Frank Freshwaters spent over half his life as a fugitive from justice. In 1957, at the age of 21, the Ohio native was convicted of vehicular manslaughter. What followed was a convoluted trip through the justice system. First, his prison sentence for the vehicular manslaughter charge was eventually suspended. Then, he returned to prison after violating the terms of his probation before finally escaping from an honor farm in 1959, having been transferred there for good behavior.
Authorities didn’t catch on to Freshwaters, who eventually settled in West Virginia, until 1975, but he caught a jaw-dropping break from West Virginia Governor Arch A. Moore Jr., who refused to extradite Freshwaters back to Ohio. U.S. Marshal Peter Elliott told CNN that Moore thought Freshwaters had been a good citizen.
Freshwaters then settled in Central Florida until 2015, when cold case investigators from the Marshals Service were able to track him down. In 2016, the Ohio Parole Authority released him from custody, granting him parole with five years’ supervision. In total, the now 89-year-old lasted 56 years on the run.
